The present invention relates to an improved composition of alditol acetal, in particular dibenzylidene sorbitol or one of its derivatives.
It relates in particular to a new powdery composition of an alkylated alditol diacetal.
It is also intended to provide a new process for improving the flow behavior and/or stability of alditol acetal compositions.
Finally the present invention also relates to use of said compositions for preparing plastics materials or jellified materials or additives intended for use in said materials.
It is well known that alditol acetals such as dibenzylidene sorbitol and its derivatives may be used as additives, in particular as nucleating agents or clarifying agents for plastics materials such as polyolefins.
These products are also used as agents for jellifying or modifying the viscosity of a variety of materials such as compositions for cosmetic or pharmaceutical use, adhesive compositions or paints. These compositions may also be shaped within other articles such as rods or sticks of glue or cosmetic materials, for example deodorants or air fresheners.
One of the main disadvantages associated with the industrial use of alditol acetals such as dibenzylidene sorbitol and its derivatives relates to the poor flow behavior of these products. This is due, at least in part, to the generally very powdery and very tacky character of these products. This produces problems during industrial operations such as transporting, crushing, bagging, metering, mixing, storing, cleansing, etc.
In particular, alditol acetal powders readily form xe2x80x9cdomesxe2x80x9d in storage tanks and/or transport piping. This prevents or impedes the routing, metering, and/or evacuation of these products when using feeding hoppers and metering systems in industrial units, for example units intended for the preparation of plastics materials or additives for plastics materials.
xe2x80x9cPlastics materialsxe2x80x9d are understood to mean in particular polyolefins, especially all polymers based on propylene and/or ethylene, polyamides, thermoplastic polyesters, vinyl resins, acrylic resins and mixtures of these.
This flow behavior problem of powdery forms of alditol acetals has not yet been resolved in a practical industrial manner, other than by manufacturers and/or users of these products using modified devices such as special pneumatic feeding systems or PTFE-lined hoppers.
In addition to the fact that these types of devIces may be costly and/or complex, they do not always prevent, the xe2x80x9cdomexe2x80x9d phenomena mentioned above or at the very least fouling problems which appear in hoppers, metering systems or, further downstream, screw conveyors supplying mixtures to preparation units for plastics or jellified materials.
Moreover, even within compositions of materials into which they can be introduced and metered in a satisfactory manner, alditol acetals may exhibit a poor dispersing capacity. This phenomenon can produce, in particular in plastics and jellified materials, a heterogeneity or some degree of degradation of the final characteristics of said materials (general appearance or organoleptic, optical, mechanical characteristics, etc).
A variety of technologies has been proposed in order to alleviate the problems mentioned above of Door dispersibility of alditol acetals, in particular of dibenzylidene sorbitol and its derivatives. For example, Japanese patent JP 60-101131 describes drying then finely crushing an alditol diacetal previously treated with terephthalic acid in the presence of an anionic surfactant.
Lyophilisation of a gel of alditol diacetal in a solvent has also been recommended, as disclosed in Japanese patent JP 62-253646. The lyophilized product thus obtained has a low xe2x80x9cafter tamping downxe2x80x9d density, that is the density is in the order of 100 g/l, and is always significantly less (by a factor of about 3) than that of the initial alditol diacetal.
More recently, patent EP 569 198 has disclosed ultrafine crushing of alditol diacetals on modified devices, for example combining a fluidized bed and a high speed turbine, in order to obtain products with an average particle size which is especially small, that is at most 15 xcexcm and preferably less than 6 xcexcm.
On reading example 2 of the above document it seems that this type of ultrafine crushing applied to dibenzylidene sorbitol with the brand name xe2x80x9cMILLAD(copyright) 3905xe2x80x9d is accompanied by a very significant reduction (by a factor of about 3.3) of the xe2x80x9cafter tamping downxe2x80x9d density (xe2x80x9cpacked bulk densityxe2x80x9d) of the product.
Still more recently, other technologies have been recommended with the objective of improving the dispersibility of alditol diacetals, in particular:
the preparation, by drying/spraying, of a fine powder based on a mixture of an alditol diacetal and a special phosphite, said mixture having been previously solubilized in a solvent (patent EP 651 006), or
forced drying and crushing, in particular in an instantaneous dryer, of damp alditol diacetal, the dried/crushed product obtained having a very low residual water content (0.01%) and an apparent density in the order of about 200 g/l (patent JP 06-048783).
The result is that the methods recommended for guaranteeing good dispersibility of alditol acetals within plastics materials etc, are generally complex and/or costly or even dangerous, in particular due to the fact that they involve the use of specific drying equipment, crushing equipment and/or solvents.
In addition, as indicated above, these methods generally have the objective of or the effect of significantly reducing the density of alditol acetals, which increases their dusty character and dangerousness (risks of explosion and inhalation) and worsens their ability to flow freely.
Another disadvantage associated with the industrial use of alditol acetals, or at least in some of them such as, for example, certain alkylated or halogenated derivatives of dibenzylidene sorbitol, originates in the unstable character of these products. This instability is exhibited in particular by odiferous problems and by a reduction in effectiveness under some conditions of use.
These problems may be detected organoleptically in the initial product, i.e. even before any processing or special use of the product.
They may be detected organoleptically only when the alditol acetal is actually used in an industrial process, for example during thermoforming of a plastics material in which alditol acetal has been incorporated.
This type of thermal treatment may, inter alia, generate, encourage or amplify decomposition phenomena, in particular hydrolysis and/or sublimation of the alditol acetal and the emission of undesirable odors, in particular of an aldehyde type.
This is particularly undesirable in the case of materials intended to be used in contact with foodstuffs, pharmaceuticals or cosmetics.
This instability, in particular thermal instability, of alditol acetals is generally accompanied by a reduction in their effectiveness as nucleating or clarifying agents, the decomposition or hydrolysis products of alditol acetals not being able to act in this way.
A variety of processes has been suggested for improving the stability, in particular thermal stability, of alditol acetals, in particular dibenzylidene sorbitol and its alkylated or halogenated derivatives, and thus for minimizing or masking, or even suppressing odiferous problems and/or problems of lowering in the effectiveness associated with the use of these products.
These problems may be due in particular to the residual presence, even within the plastics materials, of species which are capable of catalyzing the decomposition of alditol diacetals, such as residual amounts of polymerization catalysts with an acid nature, as described in patent EP 68 773.
The above patent recommends the incorporation, within particular plastics materials (low density linear polyethylenes with a high concentration of residual catalysts), of inhibitors of the decomposition of diacetals selected from a wide variety of chemical families (metal sequestering agents, amines, alkenes, epoxides, cyclic esters, etc).
It has also been proposed, as in patent EP 298 375, to treat the surface of alditol diacetals with metal salts of aliphatic acids or lactic acids with the objective of improving the thermal stability. In the examples in the above patent, 1,3-2,4-di(methylbenzylidene) sorbitol can be stabilized by hot mixing with an equivalent weight of calcium stearate, the mixture obtained being crushed after cooling before being introduced into a polypropylene resin.
Patent EP 361 087 describes the incorporation, into a crystalline polyolefin, of cyclodextrine as a stabilizing agent for dibenzylidene sorbitol or its derivatives.
It has also been recommended that a primary aliphatic amine be incorporated into polypropylene with the objective of reducing the odor generated by the alditol diacetal which it contains, as described in patent JP 4-82890.
Patent EP 522 558 describes the stabilization of dibenzylidene sorbitol and its derivatives by mixing, preferably in a solvent medium (methanol), with 0.05 wt. % to 20 wt. % of sorbic acid and/or potassium sorbate.
Patent JP 9-286788 describes the stabilization of DBS and derivatives by adding polyalcohols, this addition taking place either during the preparative process for alditol diacetal or later by a physical mixing process, in the dry or in the presence of a solvent such as water or an alcohol.
According to the above patent, in particular the examples, the polyol is advantageously introduced in relatively high concentrations, in particular at a concentration of 20% to 150% with respect to the weight of the diacetal.
Moreover, the examples always provide for the use of the polyol in a solvent, in this case isopropanol, in which the diacetal is dispersed, the latter generally being added in the form of a suspension in another solvent, in this case methanol.
The composition of this diacetal is recovered after heating and homogenizing the resulting mixture with the evaporation of any solvent used.
It seems, however, as will be examplified below, that a composition prepared in this way still has a poor flow behavior and a tacky character. In addition its aerated density is not increased in any case.
Finally, patent EP 569 198 mentioned above, relating to the sorbitol or xylitol diacetals with ultrafine particle sizes, indicates that these types of products reduce the color and odor problems in the final products. This patent is the only one which actually describes the possibility of obtaining, by applying a single process (ultrafine crushing), products which are a priori improved both in terms of xe2x80x9cdispersibilityxe2x80x9d and in terms of xe2x80x9codorxe2x80x9d.
However, as indicated above, this process involves the use of very specific crushing devices and leads to the production of powdery forms which have a very low density and flow with great difficulty.
Thus there is a need to provide a simple, non-costly and non-dangerous method allowing an improvement in the flow behavior and/or the stability of alditol acetals and which, obviously, does not damage other functional characteristics of these products and does not reduce the range of application, in particular as additives for plastics materials and jellified materials.
The Applicant has found, after a number of research projects, that such a method can comprise adding to said acetals , with certain selected compounds, that s tocopherols and their derivatives, polyols and their non-fatty derivatives and mixtures of these.
To be more specific, the present invention provides a composition of alditol acetal with improved flow behavior and/or improved stability, characterized in that it includes at least one alditol acetal and at least one additive selected from the group comprising tocopherols and their derivatives, and also polyols and their non-fatty derivatives, and that it has an aerated density greater than 250 g/l.
The alditol acetal composition in accordance with the invention can also be characterized in that the alditol acetal and selected additive such as defined above have been subjected in the presence of each other to a shaping and/or densification procedure, in particular granulation, compaction or extrusion.
The improvement in flow behavior of compositions of alditol acetals which can be obtained by using such additives may be recognized in particular by:
a less marked propensity to create domes, or to cause fouling and/or other hindrance, within classical industrial devices for storing, transporting, evacuating, metering or mixing and/or
a less marked propensity to generate xe2x80x9cfinesxe2x80x9d or dusts during handling or use.
To this end, the additives mentioned above may act as binding agents or densification agents for alditol acetals.
The improvement in the stability of alditol acetal compositions which may be obtained by using said additives can be recognized in particular by a less marked propensity, during and/or after thermal processing, to emit undesirable odors which can be detected organoleptically and/or by an even more improved transparency of the plastics materials in which said compositions are incorporated.
To this end, the additives mentioned above may also act, with regard to alditol acetals, as stabilizing agents or odor masking agents.
xe2x80x9cAlditol acetalxe2x80x9d in the context of the present invention is understood to mean in particular alditol diacetals, in particular those resulting from the dehydrocondensation in two positions of an alditol with 5 or 6 carbon atoms and a benzoic aldehyde.
Said alditol may be selected in particular from the group consisting of sorbitol, xylitol, mannitol, ribitol, arabitol and iditol. It may be modified at the level of the last carbon atom in the chain, in particular by introducing a carboxylic group and thus consists of a gluconate or a xylonate.
The benzoic aldehyde used with the objective of preparing alditol acetals which can be used in accordance with the invention may consist in particular of benzaldehyde, 1-naphthaldehyde or of any one of their respective derivatives.
In a preferential manner, the benzoic aldehyde used consists of benzaldehyde or one of its derivatives, for example those derivatives substituted in one or several positions by an alkyl, alkoxyl, hydroxyl, halcen, thioalkyl or sulphoalkyl group.
When the benzaldehyde is substituted in several positions, the substituents may or may not be identical. The substituents may also be linked to form a carbon ring.
In an advantageous manner, the benzaldehyde is substituted in one, two or three positions by an alkyl group, in particular methyl or ethyl, by a halogen group, in particular a chlorinated or fluorinated group, by a hydroxyl group and/or an alkoxyl group, in particular methoxyl. The substitution may be made in particular in positions 2 (ortho), 3 (meta) and/or 4 (para) of benzaldehyde.
The alditol acetal which can be used in accordance with the invention may be selected in particular from those described in European patents EP 286 522 and EP 421 634 and/or in any of the patents described above within the context of the present description.
The alditol acetal is preferably an alditol diacetal selected from the group comprising 1,3-2,4-di(benzylidene) sorbitol (called DBS below), 1,3-2,4-di(benzylidene) xylitol (called DBX below), and their derivatives, in particular alkylated and/or halogenated derivatives, preferably chosen among DBS and its alkylated derivatives.
In a particularly advantageous manner, the alditol diacetal is chosen from among methylated derivatives of DBS, in particular those obtained by dehydrocondensation of sorbitol and a methylated benzaldehyde, with the methyl groups in at least positions 3 or 4 of the ring (meta or para positions respectively).
The methylated derivatives of DBS comprise in particular the following products:
1,3-2,4-di(4-ethylbenzylidene) sorbitol,
1,3-2,4-di(4-methylbenzylidene) sorbitol,
1,3-2,4-di(3-methylbenzylidene) sorbitol, and
1,3-2,4-di(3,4-dimethylbenzylidene) sorbitol.
The additives which can be used in accordance with the invention with the object of improving the flow behavior and/or stability of alditol acetals are, as specified above, selected from among tocopherols and their derivatives, and polyols and their non-fatty derivatives.
xe2x80x9cTocopherolsxe2x80x9d in the context of the present invention are understood to mean in particular xe2x80x9ctocolxe2x80x9d or 3,4-dihydro-2-methyl-2(4,8,12-trimethyltridecyl)-2H-1-benzopropane-6-ol and all its derivatives, in particular alkylated derivatives, which may be of natural or synthetic origin.
Alkylated derivatives of tocol may comprise in particular methylated products which are methylated in at least one of positions 5, 7 and/or 8, of the benzopyrane ring in tocol and in particular correspond to xcex1, xcex2, xcex3 and xcex4 tocopherols and mixtures thereof.
In an advantageous manner a natural or synthetic tocopherol made up entirely or in part of xcex1-tocopherol and, in particular, constituted of natural or synthetic vitamin E, is used.
The derivatives of tocopherols may comprise esterified tocopherols, in particular those esterified in position 6 of the benzopyrane ring, which are esterifed by a variety of substituents such as acetate or succinate groups.
xe2x80x9cDerivatives of tocopherolsxe2x80x9d in the context of the present invention are also understood to mean tocotrienol and all its alkylated and/or esterified derivatives. They may be alkylated derivatives such as xcex1, xcex2, xcex3 and xcex4 tocotrienols and mixtures thereof.
The compounds and derivatives previously mentioned are largely described in the literature, for example in:
xe2x80x9cThe Merck Indexxe2x80x9d, 10th edition, 1983, pp. 1358-1360 and 1437,
xe2x80x9cVitamin E: Biological and Clinical Aspects of Topical Treatmentxe2x80x9d by K. Furuse, Cosmetics and Toiletries, Vol. 102, Nov. 1987, pp. 99-115,
European patent EP 384 472, p.3 lines 45 to 47,
these passages being incorporated into the present description.
Polyols which may be used as additives in accordance with the invention are in particular chosen from among the sugar alcohols, glycerol, pentaerythritol and their respective non-fatty derivatives.
xe2x80x9cSugar alcoholsxe2x80x9d are understood to mean the previously mentioned alditols for preparing alditol acetals, maltitol, isomaltitol, hydrogenated isomaltulose, maltotriitol, hydrolysates of hydrogenated starch, erythritol, lactitol and mixtures thereof.
The non-fatty derivatives of all these products may be produced from them by varying degrees of dehydration, condensation, polymerization, physical modification and/or chemical modification. They may consist for example of isosorbide, isomannide, sorbitan, gluconates, xylonates, dipentaerythritol, phenolic derivatives of pentaerythritol, non-fatty derivatives of glycerol such as ethoxylated derivatives, etc.
In a preferential manner, the polyols which can be used in accordance with the present invention are chosen from among sorbitol, glycerol and pentaerythritol.
According to a first variant, the alditol acetal composition with improved flow behavior and/or improved stability in accordance with the invention is characterized in that it comprises:
50 wt. % to 99 wt. % of alditol acetal(s), and
1 wt. % to 50 wt. % of at least one additive as defined above, these percentages being expressed with reference to the total weight of alditol acetal(s) and additive(s) contained in said composition.
Said composition of alditol acetal advantageously comprises 1 wt. % to 20 wt. %, preferably 3 wt. % to 20 wt. %, of at least one such additive.
The composition of alditol acetal in accordance with the invention may have a number of different solid forms, preferably a powdery and/or granular form and in particular the form of a densified or compacted powder, granules, pellets, pastilles or extrudates.
The powdery forms such as densified or compacted powders may have in particular the form of free-flowing compositions (free-flowing powders) based on particles with variable shape and dimensions and, for example, agglomerates in the form of flakes in which the largest dimension is generally in the range of about 1 mm to about 10 mm and the thickness is less than about 1 mm.
These various solid forms may besides contain other components than the alditol acetal and the additive. When compositions according to the invention are intended for the preparation of plastics materials, they may, for example, contain one or more other constituents chosen from among the additives described in the previously mentioned patents such as, inter alia, antioxidant agents, stabilizers, neutralizers, chelating agents, nucleating agents, clarifying agents, lubricants, anti-UV, antihaze agents, antiblocking agents, antistatic agents, fillers, pigments, phosphites.
The bringing into contact of the alditol acetal and the additive within the composition according to the invention may take place in a variety of manners and in particular by hot or cold mixing, generally followed by one or other of the known methods of granulating, compacting, pelletising or extruding.
The Applicant first found out that the bringing into contact of the alditol acetal and the additive could not merely result, to be efficient, from a simple physical mixing of the two constituents.
The Applicant then discovered, as will be illustrated, that it was advantageous to mix, cold, an alditol acetal such as a methylated derivative of DBS and an additive such as glycerol, sorbitol or pentaerythritol, then to subject the mixture obtained, also cold, to a compacting operation, for example using a roller compactor.
By mixing or compacting xe2x80x9ccoldxe2x80x9d, it is to be understood that the operations are performed in the absence of any external source of heat the use of which being intended to increase significantly, directly or indirectly, the temperature of the mixture. Also excluded is any operation which is intended to melt, or solubilize in a solvent, an additive which is in a solid form at ambient temperature.
xe2x80x9cAmbient temperaturexe2x80x9d is generally understood to mean a temperature lower than 30xc2x0 C., and generally in the range of about 15xc2x0 C. to about 25xc2x0 C.
In the context of the invention, the additive is preferably used in the physical state in which it is found at ambient temperature.
This method of operating at ambient temperature minimizes the risks of degradation of the alditol acetal, the energy requirement and the hazards associated with a process which would involve operations such as heating and/or the use of a solvent.
In a particularly advantageous manner, the mixture prepared and compacted xe2x80x9ccoldxe2x80x9d contains an additive which has been used in a solid form, i.e. in a form which is neither liquid nor pasty, and which is kept in this form during the mixing/compacting operations.
In a surprising and unexpected manner, the Applicant found that a solid additive (i.e. not melted nor solubilized in a solvent), amorphous or crystalline, could act, simply by applying pressure, as a binder, and enable the production of alditol acetal compositions which are simultaneously improved with respect to flow behavior, density and dispersibility.
According to the Applicant, the non-molten state of the binder seems to avoid the problems of adherence of the obtained composition to the walls of the containers used for preparing, transporting, crushing, bagging, metering, mixing, storing, etc.
The Applicant has also noticed that by proceeding xe2x80x9ccoldxe2x80x9d, in particular at ambient temperature, and by using a solid additive, the crystalline structure of the diacetal contained within the composition is not significantly modified when compared with the crystalline structure of the original diacetal, without an additive.
Conversely, it has noticed that when using a binder in the liquid, solubilized or molten state, this crystalline structure is altered to a greater or lesser extent.
For example, FIG. I represents a scanning electron microscope photograph (SEMxe2x80x94magnification 3 500) of an alditol acetal composition in accordance with the invention, obtained by compacting, on a 3-roll compactor at about 20xc2x0 C., 1,3-2,4-di(3-methylbenzylidene) sorbitol (called MDBS below) and 10 wt. % of a polyol which is solid at this temperature, in this case sorbltol.
It can be seen that the crystalline structure of the diacetal contained in the composition prepared in this way is not significantly altered since, like the original MDBS and, more generally, like methylated derivatives of DBS, this structure is largely present (i.e. more than 50% of its weight) in the form of rods with a length in the range 5 xcexcm to 10 xcexcm and the contours of which are clearly defined. These crystals, like those of the original MDBS, are not oriented in a preferential direction.
FIG. II represents an SEM photograph of an alditol acetal composition also in accordance with the invention, obtained under the same conditions but starting from MDBS and 20 wt. % of a polyol which is liquid at 20xc2x0 C., in this case glycerol.
In this case the crystalline structure of the MDBS is slightly altered and is in the form of irregular clusters, not preferentially oriented, of rods with contours which are not clearly defined and the majority of which having a length less than 5 xcexcm.
FIG. III is an SEM photograph of an MDBS composition obtained in the same manner but in which only 10 wt. % of an additive, in this case glycerol monostearate, was added in a molten form and kept in this state during the mixing and shaping operations.
In this case the crystalline structure of the MDBS is greatly altered. A crystalline magma is present, which is more or less continuous, oriented in accordance with a preferential direction and consists of elongated structures which are apparently flexible and with non-defined contours.
Consequently, the present invention also provides a process for improving the flow behavior and/or stability of an alditol acetal characterized in that it includes at least one step during the course of which said aldatol acetal is mixed cold, shaped and/or densified, also cold, and in particular by granulating, compacting or extruding, with at least 1 wt. %, preferably 3 wt. % to 20 wt. %, with respect to the total weight of the mixture, of an additive added and maintained in the solid state, said additive preferably being a stabilizing agent or an odor masker for the alditol acetal.
The present invention also provides, as a new industrial product, an alkylated, preferably methylated, alditol diacetal composition, characterized in that it:
a) flows freely,
b) contains at least one additive which:
is solid at ambient temperature,
preferably represents 3 wt. % to 20 wt. % of the total alditol diacetal and additive contained in said composition, and
c) contains an alkylated alditol diacetal most of which is in the form of rod-like crystals with a length in the range 5 xcexcm to 10 xcexcm and the contours of which are clearly defined.
The compacting operations, but also the granulating or the pelletising operations in particular, enable the production of alditol diacetal compositions in accordance with the invention with aerated densities greater than 250 g/l, and possibly reaching 700 g/l, in a simple, reproducible and cheap manner.
xe2x80x9cAerated densityxe2x80x9d is understood to mean the mass per unit volume of a composition which is measured without any tamping down or tapping. This feature is measured by allowing the composition to flow under its own weight into a 100 ml graduated cylinder through a funnel with non-rigid walls (a paper funnel).
Despite densities of this magnitude, the Applicant observed that these compositions of alditol diacetals disperse in a totally satisfactory manner within the materials in which they are introduced and then have, in a surprising manner, an undiminished effectiveness, even an improved effectiveness.
The improved alditol diacetal composition according to the invention is thus also characterized by the fact that it has an aerated density in the range 275 g/l to 700 g/l, preferably in the range 300 g/l to 650 g/l. This density may be in particular in the range 300 g/l to 490 g/l.
To the Applicant""s knowledge, a powdery composition of an alkylated alditol diacetal which flows freely and has this type of aerated density, represents a new industrial product, examples of the unexpected advantages of which will be given below.
Furthermore, the present invention also provides a powdery composition of an alkylated, in particular methylated, alditol diacetal which flows freely and has an aerated density greater than 250 g/l, preferably in the range 275 g/l to 700 g/l and in particular in the range 300 g/l to 650 g/l.
In a very advantageous manner, such powdery compositions have an aerated density in the range 300 to 490 g/l.
Alditol diacetal compositions in accordance with the invention may be used in particular in the preparation of plastics materials or jellified materials, but also in the preparation of additives intended for use in such materials.
They may be used in particular, either in the form of powders, for example densified or compacted powders, or in the form of granulates, for the preparation of additives for plastics materials being advantageously in a granular form.
These types of additives may consist in particular of ready-to-use mixtures which are in the form of free-flowing granulates containing in the final state, in addition to the alditol acetal and additive in accordance with the invention, one or more other constituents chosen from the additives described in the patents mentioned above. These types of mixtures are known to the profession by expressions such as xe2x80x9cone packxe2x80x9d, xe2x80x9ccustom blendxe2x80x9d, xe2x80x9cpcre-blendxe2x80x9d or xe2x80x9cno dust blendxe2x80x9d mixtures.
xe2x80x9cAdditives for plastics materialsxe2x80x9d are understood to mean master mixes (master batches), which have the form of granulates of plastics material, for example polypropylene, in which the additives have been predispersed, entirely or partly, before being eventually incorporated into the final product.
For whatever use the compositions in accordance with the invention are intended, in the future there will be available new methods for improving the flow behavior and/or the stability of an alditol acetal. A process may be characterized in particular in that it includes at least one step during the course of which said alditol acetal is mixed and shaped and/or densified in any manner whatsoever, in particular by granulating or compacting, with at least 1 wt. % with respect to the total weight of mixture, of an additive selected from among tocopherols and their derivatives, polyols and their non-fatty derivatives and any mixtures of these products.
Moreover it follows that the basic concept in the present invention also depends on a process for densifying and/or improving the flow behavior of a composition of preferably alkylated, even more preferably methylated, alditol diacetal, using a stabilizing or odor masking agent for said diacetal, said agent preferably being in the solid state during its use.